Triphenylphosphine → HCID 86759691, compound

HRID 2179942Notes

Reaction equation

HRID 2179942 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11])#[N:2].[CH3:12][C:13]([O:16][C:17](=[O:30])[N:18]([CH2:20][CH2:21][C@H:22](O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:19])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[O:11][C@@H:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][CH2:20][N:18]([CH3:19])[C:17](=[O:30])[O:16][C:13]([CH3:15])([CH3:14])[CH3:12])#[N:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 11043680HCID 11043680, compoundHCID 114236802-Hydroxy-4-methoxybenzonitrileHCID 14357405Diethyldiazodicarboxylate

Product 1

HCID 86759691HCID 86759691, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-cyano-5-methoxyphenol (149 mg, 1.00 mmol) and [(3S)-3-hydroxy-3-phenylpropyl]methylcarbamic acid 1,1-dimethylethyl ester (265 mg, 1.00 mmol) in tetrahydrofuran (10 ml) under nitrogen was added triphenylphosphine (290 mg, 1.10 mmol) followed by diethyl diazodicarboxylate (192 mg, 1.10 mmol). The reaction mixture was stirred at room temperature for 24 h, then evaporated to dryness. The residue was eluted down a flash chromatography column using 30% ethyl acetate/isohexane as eluent to give 275 mg (69%) of the subtitle compound as an oil.

Workup

  1. customevaporated to dryness
  2. washThe residue was eluted down a flash chromatography column

Sources & evidence

ORD record
ord-e9ffc4fc351846e3a935ffe3f947caba
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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